The enigmatic Chief of Surgery at Seattle Grace is a leading figure in the show. Always vigilant, seeking and trying new things, his ambition is to see Seattle Grace as the top surgical program in the country. This sometimes leads him to take daring decisions, at the beginning of the first season the Surgical Program is presented as one of the best in the United States. Later in the series his wife Adele asks him to retire, forcing him to choose between his career or their marriage. He tries to skirt around it, but Adele, tired of waiting, makes her choice and leaves him. He moves out and sleeps in his office for a short time. Since learning of Ellis Grey's illness, Richard had been visiting her regularly, but upon deciding to attempt a reconciliation with Adele, he realizes that he can no longer continue his emotional affair with Ellis. He attempts to patch things up with his wife, but is stunned to find out that she has apparently moved on to someone else. In the meantime, Richard makes plans to retire and must name his successor. He first thought of recommending Dr. Preston Burke as his successor, but after the secret of Burke's tremor and cover-up came out, that plan is put to a stand-still. Nevertheless, he tells the hospital board of his retirement but has yet to name his successor; Dr. Derek Shepherd, Preston, Dr. Addison Montgomery and Dr. Mark Sloan are all eagerly clamoring for the post. Richard eventually chooses Derek, but Derek tells him that Richard should remain chief.
Near the end of the third season, Adele is admitted to the hospital and is discovered to be pregnant (at 52 years old). Though he believes the father to be the man Adele insinuated to be seeing months earlier, Richard stays by Adele's side as she is treated. However, due to complications, she loses the baby. Adele later admits to Richard that the baby, which was a boy, was actually his. At the conclusion of the third season, Richard and Adele decide to give their marriage another try.
At the beginning of the fourth season, Richard and Adele declare that his work is the reason that their marriage has failed and separate. He consequently moves in with his friend Derek Shepherd in his trailer home and tries to repair his life as a divorcé for the remainder of the season until, by the end, he reasserts his good reputation to his wife and wins her back.
At the start of the fifth season, Richard starts to deal with the fact that Seattle Grace's surgical program ranking has been suffering. Determined to repair his hospital's reputation, he has become determined to enforce a new tougher series of hospital rules. Adding to his new behavior, he seems to becoming more and more agitated by Meredith Grey's (Ellen Pompeo) presence in his life as she is a reminder to him of every mistake he has made over the years. Over the course of the season, he becomes resentful of his mentee in General Surgery, Dr. Bailey's decision to leave the General Surgery program to embark upon a fellowship in Pediatric Surgery and attempts to prevent it in any way possible; he gives her an uninspiring letter of recommendation and buys a surgical robot for General Surgery to "lure" Dr. Bailey back to the program. However, as he finally comes to terms with Dr. Bailey's choice, she confides to the Chief that her husband has left her with an ultimatum - if she takes the fellowship in Pediatrics, he will divorce her. Dr. Bailey tells the Chief that she has decided that she will leave her husband herself, but that she still cannot take the Pediatrics fellowship, because she will now be a single mother.
In the sixth season he has been under a lot of stress. In the episode "New History" most of the people believe he is having an affair due to his odd decisions and mistakes lately, but it is revealed at the end of the episode that the chief has gone back to drinking again. At first, he tells Meredith, who he has taken under his wing to help out learning new skills, that he wasn't an alcoholic, but rather in a state of depression, and he promised that his eggnog at Christmas would be his last drink. However Meredith discovers him at the bar very drunk, showing that he has indeed relapsed. He was given the choice by Derek and the Board, to retire early or enter a rehab program where he would receive help for his drinking, and possibly gain his job back. Richard contemplated throwing away his career, which caused him and Derek to get in a shouting match. He later handed Derek the papers agreeing to enter Rehab. After rehab, Richard returns as a General Surgery attending and performs awake surgery on Harper Avery. On the day of shooting, he enters the hospital against police orders and convinces Gary Clarke to shoot himself.
Following the shooting, Derek impulsively quits as Chief and Richard is re-instated. It appears that his wife Adele is starting to show early symptoms of Alzheimer's and he starts a diabetes clinical trial based on Ellis' diaries. When he asks Meredith to be a part of his trial, she declines and joins Derek's trial on Alzheimer's instead. Adele later receives a spot on Derek's trial. During the trial, Meredith tampers with the drugs so that Adele does not receive the placebo. After the truth is revealed which causes Meredith to lose her job, Richard takes the blame and steps down as chief of surgery to protect her, being replaced by Dr. Owen Hunt. As Adele's condition deteriorates, Richard is forced to have her placed at Rose Ridge. Catherine Avery comes to Seattle and develops an interest in Richard but he refuses her advances because he is a married man. However, discovering that Adele, who does not recognize him anymore, has started a relationship with a new man at Rose Ridge, he lets her go. In season 8 Richard and Catherine run into each other in the hotel where they are staying
while in San Francisco to serve as examiners for the boards and have a one-night stand. However, Catherine's son Jackson, who was also there to take his boards and worked under Richard at Seattle Grace Mercy West, is horrified after finding out about the relationship.
While on the way to Bailey's wedding, Richard gets a phone call alerting him that Adele has been rushed to the hospital. Bailey and Meredith perform emergency surgery, which was successful. However, it is revealed that Adele died of a heart attack while recovering in the ICU. He later embarks on a relationship with Catherine.
A storm hits the hospital and creates a power outage. After operating on a former case of Bailey's, he goes in the electrical room and finds the man who was in charge of the generators lying on the ground. He sends him to an OR and stays in the room to restore the power but is seemingly electrocuted.
Richard slowly recovers from being electrocuted after putting Meredith as his POA. Richard returns to work and is given a retirement package from Hunt on his birthday. Richard accepts to become the head of the residency program mentoring the residents. He continues his relationship with Catherine and plans to propose. Richard chats with Dr. Maggie Pierce after her first day at Grey Sloan Memorial who says that it was surreal to work at a place where, Ellis Grey, her birth mother, has the same name. Maggie bears a striking resemblance to Richard, suggesting that he is her father.
As series 11 progresses, it is revealed through moments of flashbacks from Meredith that Maggie is in fact Richard's daughter, and that Ellis gave her up out of shame and suffering from depression. Upon finding out the truth Richard doesn't tell Maggie the news straight away out of fear Maggie will reject and blame him for giving her up. This causes Richard to act strangely around her, causing Miranda Bailey to wonder if he is sleeping with her, Richard correcting her on this mistake causes other members of staff to find out the truth before Maggie. After the truth is revealed Maggie is angry with Richard and ignores and rebuffs him for some time. Later on in the season the pair are seen to have bonded and are now friends, with Richard and Meredith sharing stories with Maggie about Ellis.
In the season 13 episode "The Room Where It Happens," when a male patient is wheeled into the OR where Meredith, Hunt, and Edwards are waiting, Webber shows up to help having napped all day. Webber wants the patient to be given a name, he picks Gail, a cello player and music teacher. During the episode, each of the doctors has a flashback to a tragic incident from their past. We learn near the end of the episode, Gail was Webber's mother, who had advanced pancreatic cancer and died when he was ten.
He got better lately tho maybe I'll plus later